101 New York Dates
by Vesper212
Summary: Future fic! Kurt and Blaine are going to school in New York and they are practically neighbors! Where would they go for their dates? Each chapter depicts one date around town. My Klaine guide to a romantic New York City.


**101 New York Klaine Dates**

**Chapter One: Long Walks, Dinner & Dessert**

**A/N:** Watching the Glee finale made me realize how much I miss Manhattan *sob*. So I've decided to relive my life through Klaine! All the places referenced here (except for the gay club) are actual places in New York City. Fluff galore and rating will likely go up to M – there are just too many perfect places in NYC for Klaine to get their sex on. Feel free to give me ideas for future dates!

**Disclaimer:** Don't own Glee and this is not an official guide so I do invoke creative license on the settings.

* * *

><p>Kurt was in his room practicing his breathing techniques when his phone rang. The Teenage Dream ringtone blazing as he tried to fish out the phone in his messenger bag.<p>

"Oh my god!" Kurt's sleeping roommate, James, crushed a pillow on his face and exclaimed, "Kurt what is with you and oldies!"

"This song is a classic, not an oldie!" Kurt rolled his eyes before he picked up his phone. "And wake up, James, it's 3 o'clock in the afternoon!"

James ignored Kurt and pulled the covers over his head.

"Hey, Beautiful." Kurt's heart fluttered. No matter how many times he hears his boyfriend's voice on the other line, Blaine can always make Kurt giddy like a little school girl.

"So? How did your midterm go?" Kurt asked.

"Well, other than the fact I now have Plato and Socrates oozing out of my ears, I would say it went pretty well."

Blaine's voice is always so warm and comforting, Kurt thought as he looked out his window down Broadway, toward the Columbia campus. "Well, consider the fact that David practically gave you all the questions, I would expect nothing less than an A from you," Kurt teased.

His boyfriend's laughter was distinct on the other end of the line. "David seems to think I am going to join him as his straight-A pledge buddy. I just can't seem to extricate myself from his high standards!"

"Standards? Blaine Anderson? What standards? Last week you got your TA to give you a one week extension by batting your eyelashes at her!"

"Kurt I can't believe you are still giving me a hard time about that, I really needed that extension!"

"Psst, whatever," Kurt rolled his eyes. "So are you still planning to rehearse with your band this afternoon? Have you guys resolved your Yoko Ono problem?"

"Actually, that's what I'm calling about. Well, to answer your question, that would be a no. Julie still has our drummer on a tight leash so he had to cancel tonight. But the good news is, now my day is completely open!"

"Yeah? So?" Kurt knew what Blaine is about to propose, but there is no reason to make it too easy on his boyfriend.

"Oh com'on, Kurt!" Blaine is always easy to bait. "We like haven't gone on a proper date for like ever!"

"You seem to forget that we have coffee together every day, Blaine." Kurt tried to hide his smile in his voice. "You know I have to practice."

"It's Thursday, Kurt, you don't have any classes tomorrow. You can practice from morning to night." Blaine said. "Plus I thought you hate the Hungarian Café."

"I _do_ hate the Hungarian Café!" Kurt's blood pressure started to rise as Blaine brought up one of his favorite rant subjects. "The amount of tweed in that place is atrocious and do not get me started on the improper lighting…"

"Kurt, calm down!" Blaine can be heard chuckling. "How about.. to make up for the many times I made you go to the Hungarian Café with me, I take you out for a relaxing dinner tonight?"

"Well, I don't know…" Kurt loves to hear Blaine beg.

"Pretty please? How about if I throw in dessert as well?"

"Fine, I guess I should indulge you once in a while."

"You know you spoil me, Kurt."

"So where do you want to go? And if you say yakitori again I am going to hang up on you."

"What are you saying?" Blaine sounded hurt. "How can you not like meat on a stick?" Blaine's voice suddenly dropped an octave lower, "At least that's not what you said last weekend when you went down on me…"

Kurt blushed furiously and quickly looked over at James to make sure his roommate was still curled up under the covers.

"Blaine, one more word from you and I'm going to…"

"Whoa, whoa, let's not use the no-sex card on me again, okay? I promise to behave," Blaine quickly interjected. "I actually have something different in mind. Are you in the mood for a stroll? It's such a nice day outside."

Kurt knows why Blaine loves to take walks with him, and bit his lips in excitement at the thought of it. They've learned from their days in Ohio to not display excessive PDA in public places, or even at home when other people are around. But now that they are in New York, every once in a while, they just like to take long walks down a bustling street together, hand in hand, alone together in the crowd.

Klaine smiled as he remembered the last time they went on a double date with Rachel, who is now at Julliard: "I think Blaine just wants to show you off," Rachel whispered in Kurt's ear, feigning disgust at Blaine's wide smile as people on the street pretend not to ogle at the boyfriend he had linked in his arm. She added, "It goes along with his attention-whore personality. As someone who has had a spotlight shone on them since birth, I would know."

"Kurt? Are you still there?" Blaine's voice brought Kurt back into the present.

"Sure, I think a walk would be really nice. Where are we going?"

"Just meet me outside the gate in 10 minutes. It'll be a surprise."

"Blaine, I think you meant to say 'meet me outside the gate in 1 hour'," Kurt corrected Blaine as he approaches his closet.

"My bad. Kurt, would you kindly please meet me outside the gate in 1 hour?"

* * *

><p>As Kurt approached Columbia's Broadway side gate, he could see Blaine's silhouette leaning against the stone column, and for a moment Kurt just felt so thankful for having Blaine in his life. Blaine, who heartily agreed to come to New York with him for college, who drove half way across the country from Lima to New York to help Kurt move into his new school, and who has done everything to make his new life in New York fun and exciting.<p>

As if sensing Kurt's presence, Blaine looked up and met Kurt's gaze, his eyes immediately lighting up. "Hey!" Blaine ran toward Kurt and gave the countertenor a big hug. "Com'on, we need to get out there while it's still bright!" He grabbed Kurt's hand and started to run across the street and down the stairs into the subway station.

The train was crowded as usual, and as random strangers began to pack themselves in like sardines, Kurt quickly stepped against a fiber glass partition, and Blaine followed by standing in front of Kurt with his arms protectively on the wall around him. The pair has spent so much time on the subway together that this has now become a game they play. Blaine hates to see Kurt pressed against other strangers, so Kurt always seeks out the nearest wall so that Blaine can shield him.

Plus their game only gets better when there is practically no breathing room on the train. With each stop, as more people filed into the train, Blaine had to press himself closer and closer on to Kurt, until finally, their lips were practically rubbing against each other.

The corner of Kurt's mouth began to rise as he felt something hard pressing up against his thigh, "Why mister," he whispered in Blaine's ear. "Are you sexually harassing me on a crowded subway train?"

Before Blaine can respond, the lady pressed up behind Blaine screeched in a voice that the whole train can hear, "Oh hell no! If I ain't getting any on this train, you sure as hell ain't getting any on this train!"

As snickers, whistles, and catcalls began to fill up the car, a very red Kurt and Blaine was saved by the fact they have finally reached their destinations stop. The boys quickly exited the train before the tourists can whip out their camera phones.

When they came up from underground, Kurt noticed that they were near Lincoln Center, and practically in front of Julliard. "Are we doing a double date with Rachel again?"

"No, trust me," Blaine grabbed Kurt's shoulder and began to usher him down the street. "It's a surprise, remember?"

As the pair trekked westward, Kurt was becoming more confused. Though they were just a block from Lincoln Center, all the pedestrians and stores have practically disappeared. The streets looked empty, and the architecture bleak and desolated.

"We are close!" Blaine said as they approached an abandoned looking industrial site below the Westside highway.

"Ugh…" Kurt stalled his steps and gave Blaine his best 'bitch please' look. "Blaine, are you playing out one of your kinky fantasies again? I am not having sex with you on top of rubbles in an abandoned lot underneath the highway. Kurt Hummel will not role play as a homeless person!"

"What?" Blaine shook his head as he reached for Kurt's hand. "No, Kurt, I want to show you Riverside Park! My aunt used to take me here to ride my bike when I was a kid!"

Blaine's Aunt Nora, a famous novelist, has a spacious apartment on Central Park West, and has always invited Blaine to visit her whenever she decided to grace the apartment with her presence. But with Nora now favoring the more temperate climate of North Carolina in her old age, the apartment has been left empty for some time. Blaine already suggested that after their freshman year, they should just move in the apartment together.

"There is a park here?" Kurt cocked his eyebrow. "I don't see a park at all."

"Oh there is definitely a park here," Blaine began to lead Kurt down a flight of stairs. "You'll see."

After zigzagging their way through the concrete wasteland beneath the highway, Blaine stood on top of a flight of stairs and pointed westward. "Look, Kurt!"

Kurt's heart nearly stopped at the breathtaking scenery that appeared in front of him. From their elevated vantage point, Kurt could see the light blue water of the Hudson River glistening against the afternoon sun, and on top the soft waves were various white sailboats, moving up and down the river. All along the water edge of the park, which curves around the New York side of the Hudson River Valley, are various piers and docks lined with small boats. Kurt could even feel a light sea breeze in the air, and marveled at the meticulously groomed trees swaying along the parkway.

"Are we still in New York?" Kurt was having a hard time adjusting to the radical shift from the typical chaotic and noisy New York to this serene, tranquil New York.

"Come, Kurt," Blaine led Kurt down the stairs. "Let's go out on the marina."

As the two boys stood side by side on the edge of the extended marina, practically in the middle of the Hudson River, Blaine gently laid his hand on top of Kurt's on the railing. Behind them a few toddlers were running around on the pier, giggling and playing with their adults. Kurt closed his eyes, feeling the tender breeze caress his face. He could smell the water swaying beneath them, and hear the seagulls calling in a distance.

When he opened his eyes, he saw that Blaine has been watching him.

"Happy?" Blaine smiled.

"Happy." Kurt smiled back.

* * *

><p>As the pair walked up Riverside Park, Blaine tried to tell Kurt about where he plans to take them for dinner. "It's only a couple of blocks up," He pointed to an aqueduct-looking stone structure not far up the riverbank.<p>

"That's a restaurant?" Kurt mused, still reveling at the fact that they are holding hands and not one person around them seems to care.

"Yeah, it's the Boat Basin Café." Blaine explained as he unconsciously pressed his shoulder against Kurt. "It's only open a couple months out of the year. The food is very simple, but the view is amazing. You can boat-watch up and down the Hudson River while enjoying cheese burger and fries. It's great!"

After walking up a spiral limestone stairway, the pair was quickly seated at a table overlooking the river and the Jersey skyline. When the waiter brought them Blaine's burger and Kurt's salad, Kurt noticed that Blaine was not kidding when he said simple. The food and drinks were served on paper plates and plastic cups, and the food looked like it was prepared out of someone's backyard.

But Kurt didn't even need to bite his tongue. As he watched Blaine enjoy his burger against the backdrop of the Hudson River Valley, the river sparkling all around him, Kurt thought that he was staring at a painting. Kurt smiled, and etched this moment of perfection in his mind.

Just as Kurt thought the day can't be more beautiful, he noticed that the sky had changed from bright blue to a deep orange as the light slowly dimmed around them.

Blaine leaned forward, his eyes shimmering in the twilight, "Let's order some nachos and eat it while we watch the sunset!"

Kurt could have pointed out so many things that are wrong with the first part of that sentence, but he was too blissful to care. He was going to share a sunset with his boyfriend, and he might even try one of those things if that's what it takes. So Kurt nodded, and proceeded to watch his boyfriend finish the entire plate of nachos as the sun, accompanied by a spectacle of brilliant colors, slowly disappeared behind the Jersey skyline.

* * *

><p>When Kurt and Blaine reemerged on the busy streets of the City, it was already night time.<p>

Blaine looked at his watch, and was practically hopping as he turned to Kurt. "We have perfect timing! Do you mind if we just head directly to the dessert place right now?"

"I don't know," Kurt looped his arm into his boyfriend's as they continued walking away from the cafe. "I think dessert is too much for me right now."

"Oh but Kurt we have to do this," Blaine began to pout. "They have great coffee, too. You won't regret it. It's just a few blocks from here."

Kurt knows he can never say no to a pouting Blaine, so he nodded, and let Blaine guide him toward a street lined with brownstones.

It wasn't hard for Kurt to spot where they are going. Down the end of the dark block, there was one single spot where warm golden light was pouring on to the street through a bay of windows. To contrast the gold, the tall trees in the walkway in front were adorned with blue Christmas lights, each sparkle dazzling against the darkened street, resembling a galaxy of stars.

As Kurt and Blaine stood in front of the elevated restaurant, looking up at its European design and floor-to-ceiling French windows, Blaine circled his arm around Kurt's willowy waist and whispered, "It's not exactly Paris, but it's pretty close."

"What is this place called?" Kurt asked.

"Café Lalo. Come," Blaine scooted Kurt to a particular angle in front of the restaurant. "Do you not recognize it?"

The narrow French windows have all been opened, creating a clean and airy atmosphere, and Kurt could see the small marble tables and brown cafe chairs inside. The exposed red brick walls were lined by Cappiello posters and… Kurt sudden realized where he's seen this place from. "Oh I see, it's the café from You've Got Mail."

"Yeah," Blaine was suddenly a bit unsure, hoping Kurt won't find this place too cheesy. "And they do have good dessert. What do you think?"

"I think you are adorable, Blaine Warbler," Kurt mused as he began to ascend the stairway into the café, and Blaine happily followed.

After they placed their orders, the bubbly waitress brought out their cappuccinos immediately and Kurt and Blaine quickly settled into various conversations. While the boys go to different schools, they are in fact only living a few blocks apart, as Columbia and the Manhattan School of Music are practically next to each other. With each person's school lives undoubtedly unique, seeing each other every day, like they did in Dalton and then in McKinley, has been their one true constant. Despite Kurt's disdain for the Hungarian Café, their daily cup of coffee together is their sacred moment to share their day and to just be with each other. And despite knowing each other's life stories in digital detail, Kurt is always comforted by the fact that they seem to never run out of things to talk about.

But even though Kurt would happily just sit and chat with Blaine for hours, he nevertheless noticed that it's been 40 minutes and the waitress still has not brought out the cake and mousse they ordered. The cake was sitting and waiting in the refrigerated display case, so Kurt knew they are not still baking that thing. _Are they picking the coco beans to make my chocolate mousse? _Kurt wondered as he mentally prepared to get his bitch face on.

Stopping Blaine in mid conversation, Kurt signaled to their waitress, who seemed to be staring idly into the abyss. It took a while for Kurt to get her attention, but it was pretty obvious that no one ignores Kurt Hummel.

"Can I help you?" The waitress walked to their table. The café had become quite busy since Blaine and Kurt arrived, and she had to squeeze her way through the packed tables to get to them.

"Yes, can you please check on our orders? We've been waiting for about 45 minutes," Both Kurt's chin and eyebrows were tilted, showing off Kurt's undeniable diva presence.

"Um, okay, no problem. I'll go check on that for you." The girl quickly darted off, almost knocking a water glass off the next table.

"I'm so glad you said something," an impeccably dressed elderly lady sitting at the next table leaned over and said to Kurt. She gestured at the person sitting across from her. "My daughter and I have been waiting here for an hour!"

"Oh this is so unacceptable." Kurt raised a finger to signal his dismay, and the two ladies nodded as if they have just found their true best friend.

When the waitress returned, Kurt was immediately turned off by the fact that she didn't even bother to squeeze her way through the clustered tables. The waitress simply yelled at Kurt from a couple of tables away. Well, spoke, Kurt mentally corrected himself, since there are only about 10 tables in the entire café.

"I'm sorry, but we don't seem to have your order. What did you order again?"

"Okay," Kurt got up, and started walking toward the waitress. "We are going to fix this right now."

_Oh Kurt is so in his element right now... _Leaning into his hand, Blaine was completely smitten by his take-no-prisoner boyfriend as Kurt charged toward the waitress, easily gliding between the cramped tables. Then, as Kurt began to cuss out the waitress in front of the whole restaurant in perfect French, Blaine's eyes became practically heart shaped. _How did I become such a lucky man? _Blaine swooned.

* * *

><p>As Blaine and Kurt walked out of Café Lalo, Blaine was holding a large paper bag. "Wow, I have never walked out of a restaurant with a free cake before," Blaine exclaimed. "And it's lemon chiffon!"<p>

"Well, consider it a present." Kurt rolled his eyes, but chuckled at Blaine's puppy-like giddiness.

The boys were barely a few meters away from the restaurant when a man called out behind them.

"Wait, gentlemen, please wait up!"

Kurt and Blaine turned around to find a stubbly looking man in a wrinkled suit running toward them. Blaine remembered the guy from inside the Cafe. Stopping in front of Kurt, the man reached into his pocket and handed Kurt a business card.

Blaine leaned over Kurt's shoulder to examine the title underneath the name. In bold letters, the title stated: Associate Manager, Black Orchid Lounge.

Blaine furrowed his brows and grabbed Kurt by the elbow. "Com'on, Kurt, let's go."

"Wait," Kurt was curious, and stubborn. He looked at the card in his hand, "What is this for?"

Blaine was practically hissing at the man as the latter began to speak. "Well, I help manage a private nightspot on East Houston. We have a very exclusive clientele." He paused, noticing that Blaine was about to pounce on him any moment. "Well… ugh, we would love to have someone like you. We do everything legal, by the way. And we pay very well. Even our waiters make really good money… so if you are interested…"

"No, we are definitely _not_ interested," Blaine took the card out of Kurt's hand and pushed the countertenor behind him.

The man looked startled as Blaine shoved the card against his chest. "Look, take this and stay away from us, and do not ever come near my boyfriend again, do you hear me?"

Blaine grabbed Kurt and took off down the street.

"Okay, stop," two blocks later, Kurt pried his hand free of Blaine's grasp and forced his boyfriend to look at him. "Are you going to explain to me what just happened?"

"Kurt, the Black Orchid is some seedy gay club down on the lower east side," Blaine's disgust was visible on his face. "I can't believe that man can be this bold, I mean, that's practically soliciting!" Blaine's blood was boiling again as he imagined his innocent boyfriend being lured to one of those places.

"Wait, I still don't get it." Kurt asked. "What does he want from me?"

"Obviously he wants you to work there, and do god-knows-what," Blaine was practically spitting out the words. "I mean, I have a classmate at Columbia who works as a stripper on the side, but this is not something we want to get involved in."

Facing Kurt, Blaine looked intently into the countertenor's eyes. "Kurt, please trust me. If you ever see that guy, just stay away from him, okay?" Leaning in for a chaste kiss, Blaine whispered, "I love you."

Kurt hugged Blaine back, and whispered, "I love you, too."

* * *

><p>Later that night, the two boys were lying together in Blaine's bed, limbs tangled. Blaine was just about to drift off to sleep when Kurt suddenly had a revelation.<p>

"Wait a minute, did that guy just asked me to work as a whore?" Kurt's eyes were wide as he sat straight up from the bed, nearly knocking Blaine to the floor.

"What?" Blaine tried to burrow himself back in the pillows.

"Look at me, Blaine," Kurt grabbed Blaine's face and jolted his boyfriend wide awake. "Did that guy just insult me without me knowing?" Kurt looked like he was about to go tear someone from limb to limb.

"Well, actually, Kurt, if you think about it, it's actually more like flattering you." Blaine rolled onto his back as he rubbed his eyes.

"Explain yourself, Blaine." Kurt demanded.

"Kurt," Blaine propped himself up on one elbow. "Look, sometimes I think you are the only person on this entire planet that doesn't know how sexy you are. I mean, I am definitely pissed off at that man, but… I can also see why he wants you to work for him." Blaine's heart ached as he spoke, "If you ever walk into one of those gay clubs, you'll know. You can have any one you want and they will be literally eating out of your hands."

Blaine sighed.

"Is this why you would never take me to a gay bar?" Kurt asked softly, his eyes fixed on Blaine.

Blaine buried his face in his hands. "I'm sorry, Kurt, I know I am the biggest selfish asshole in the world. It's just… we are not in Lima anymore. This is New York and there are so many eligible men and you can have any one you want. What if you find someone else, someone perfect…" Blaine's voice cracked.

"Oh Blaine," Kurt wanted to scold Blaine for being so foolish, but instead just wrapped his arm around his boyfriend, planting soft, comforting kisses around his face.

"You always ask me to trust you," Kurt spoke in between the delicate kisses. "So I am asking you to trust me, too." Kurt looked into Blaine's eyes. "I love you, and no gay bar or silly manager is going to stand in the way of that. So trust me, Blaine Warbler."

Blaine smiled, and returned the embrace.

* * *

><p><strong>Post Note:<strong> Wow, I never knew I was capable of such sappiness. I nearly gave myself a toothache writing this. By the way, the Black Orchid Lounge doesn't really exist in NYC. I have another club in mind but naming it would be too clichéd. If you want the lounge to make an appearance in future chapters, definitely let me know in your review.

PS: Written in celebration of Chris Colfer's 21st birthday.


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